Facile synthesis and structure of novel 2,5-disubstituted 1,3,4-selenadiazoles

Guoxiong Hua, Yang Li, Amy Fuller, Alexandra Martha Zoya Slawin, J Derek Woollins

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71 Citations (Scopus)

Abstract

The reaction of hydrazide with carbonyl chloride in the presence of sodium carbonates leads to the corresponding 1,2-diacylhydrazines [1at, R1C(O)NHNHC(O)R2, R1 = aryl, R2 = aryl or alkyl] in moderate to excellent yield (57–90 %). The latter reacts with 2,4-diphenyl-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent, WR) in refluxing toluene to give a series of new 2,5-disubstituted 1,3,4-selenadiazoles (2at, 51–99 % yield). All compounds were characterized spectroscopically and six compounds were characterized crystallographically.

Original languageEnglish
Pages (from-to)1612-1618
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2009
Issue number10
DOIs
Publication statusPublished - Apr 2009

Keywords

  • Selenium
  • Organoselenium chemistry
  • 1,3,4-Selenadiazoles
  • Woollins' reagent
  • Ray crystal-structures
  • P-SE anions
  • Organoselenium compounds
  • Selenium heterocycles
  • Lawessons reagent
  • Acidic media
  • Mild-steel
  • Derivatives
  • 1,3,4-thiadiazoles
  • 1,3,4-oxadiazoles

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